US3649618A - Certain 1-aralkyl azetidines - Google Patents
Certain 1-aralkyl azetidines Download PDFInfo
- Publication number
- US3649618A US3649618A US77754A US3649618DA US3649618A US 3649618 A US3649618 A US 3649618A US 77754 A US77754 A US 77754A US 3649618D A US3649618D A US 3649618DA US 3649618 A US3649618 A US 3649618A
- Authority
- US
- United States
- Prior art keywords
- dimethyl
- azetidines
- compounds
- methyl
- azetidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
Definitions
- This invention is directed to novel series of chemical compounds, and more particularly, to a novel series of substituted a-methylphenethyl azetidines.
- the compound of this invention may be generally represented by the structural formula CH CH wherein R and R are the same J1 dilferent members of the group consisting of hydrogen, chlorine, fluorine and trifluoromethyl.
- R and R when taken together at the 3- and 4-positions respectively, may form a cycloalkyl ring having from 3 to 5 carbon atoms and when taken together at the 4- and 5-positions respectively, may form a methylenedioxy ring system.
- These compounds may be prepared as the free bases, or more conveniently, as the pharmaceutically acceptable acid-addition salts.
- salts refers to the non-toxic salts which are prepared by reacting the free base with an organic or inorganic acid.
- Representative salts include the hydrochloride, hydrobromide, sulfate, bisulfate, acetate, valerate, oleate, laurate, borate, benzoate, lactate, phosphate, tosylate, citrate, maleate, 'fumarate, succinate, tartrate and the like.
- these compounds are prepared by reacting an appropriately substituted a-methylphenethyl-3-halo-2, Z-disubstituted propionamide with a reducing agent in an inert solvent. This reaction results in a cyclization of the terminal portion of the molecule forming the azetidine compound.
- the disubstituted propionamide intermediate compounds have the general structural formula "nited States Patent O such N-substituted-3-halo-2,2-dimethyl may be prepared. Table I following below contains a few 3,649,618 Patented Mar. 14, 1972 ice wherein R and R are as previously defined and R is a member independently selected from the group consisting of alkyl and aryl.
- These compounds are prepared by reacting an appropriately substituted ct-methylphenethyl amine with a halo-2,2-disubstituted propionyl halide.
- the reac tion may be represented as follows:
- the intermediate compounds are prepared by reacting a substituted ot-methylphenethyl amine with a halo-2,2-disubstituted propionyl halide wherein the disubstitution may be with alkyl, aryl or an alkyl group and an aryl group on the 5 carbon atom.
- the propionyl halide derivative having methyl as each of the R substituents is most conveniently utilized since this acid is commercially available. It is to be understood, of course, that the reaction will proceed as set forth herein where each R is selected from either alkyl or aryl.
- Example 1.3-chloro-2,2-dimethyl-N- [a-methyl-3- (trifluoromethyl phenethyl] propionamide To a chilled mixture of 40.5 grams (0.2 molar) of ozmethyl-3-trifiuoromethyl-phenethylamine, 20.2 grams (0.2 molar) of triethylamine and 500 ml. anhydrous ether is added 31.0 grams (0.2 molar) of fJ-chloropropionyl chloride dropwise with stirring. The mixture is stirred in the cold for 2 hours, washed twice with water, and the ether layer dried over anhydrous magnesium sulfate. The drying agent is removed, the ether stripped and the crude residue air-dried.
- the crude product is further purifiedby taking same up in ether, washing the ethereal solution with 50 ml. of 3% hydrochloric acid, then with water, then with 50 ml. of 3% sodium hydroxide solution, and finally again with water.
- the ethereal solution is then' dried over anhydrous magnesium sulfate. The drying agent is removed, the ether stripped and a water-white residue crystallizes slowly on chilling; yielding 61.5 grams of 3-chloro-2,2-dimethyl-N- [ct-methyl 3 (trifluoromethyl)phenethyl]propionamide having a melting point of 5860 C.
- Example l0.-1-(phenylisopropyl)-3,3-dimethylazetidine A solution of 37.2 grams (0.125 molar) of 3-bromo- 2,2-dimethyl-N[a-methylphenethyl]propionamide in 450 ml. of anhydrous ether is added dropwise to a suspension of 9.5 grams (0.25 molar) of lithium aluminum hydride in 100 ml. of anhydrous ether at a rate to maintain reflux, and stirred at room temperature for 5% hours.
- the lithium aluminum hydride complex and excess lithium aluminum hydride are decomposed of dropwise consecutive addition of 9 ml. of water, 9 ml. of 15% sodium hydroxide solution and 27 ml.
- a number of other azetidine derivatives may be prepared having one or more radicals substituted on the phenyl ring.
- Table fumarate, oxalate, and other such acid-addition salts may be prepared.
- the test procedure utilized to illustrate this bio logical activity is relatively simple. Two groups consisting of four rats each are placed on a five-hour feeding schedule; that is, the total feeding period for a 24 hour period is 5 hours for each group at the same time of the day, seven days a week. Approximately /2 hour before the feeding time is to commence, the control group is administered a standard dosage of saline solution and the test group is administered a dosage of one of the test compounds. A measured amount of feed is given to both groups (the same amount for each group) and at the end of the 5 hour feeding period, the food remaining is measured to determine intake.
- the column headed LD mg./kg. in Table 111 above indicates the oral disage in milligrams per kilogram of body weight, which is lethal to 50% of the test animals.
- the test compounds were administered via the oral route, although other routes of administration, such as subcutaneous, intraperitoneal, and intra- TABLE II Analysis Calculated Found Empirical Compound formula B.P. 111C. 0 H N H N 1-(4-chlorophenylisopropyl)-3,3-dimethyl azetidine CnHmOlN 110-124 at 1.1 mm. pressure..- 70.72 8. 48 5. 89 70.
- the compounds were administered in the form of their hydrochloride acid-addition salts for the reason that these salts are very water-soluble and therefore CH CH CH-N l CH wherein R and R are each members independently selected from the group consisting of hydrogen, chlorine, fluorine, trifluoromethyl, and R and R taken together at the 4- and 5-positions forming a methylene dioxy ring, and R and R taken together at the 3- and 4-positions forming a cycloalkyl ring having from 3 to 5 carbon atoms; and the pharmaceutically acceptable acid-addition salts thereof.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A NOVEL SERIES OF SUBSTITUTED 1-(PHENYLISOPROPYL)-3,3DIMETHYL AZETIDINES USEFUL AS APPETITE DEPRESSANTS.
Description
U.S. Cl. 260--239 A 4 Claims ABSTRACT OF THE DISCLOSURE A novel series of substituted 1-(phenylisopropyl)-3,3- dimethyl azetidines useful as appetite depressants.
CROSS-REFERENCE TO RELATED APPLICATIONS This application is a continuation-in-part of copending U.S. Ser. No. 684,492, filed Nov. 20, 1967, and now abandoned.
DETAILED DESCRIPTION OF THE INVENTION This invention is directed to novel series of chemical compounds, and more particularly, to a novel series of substituted a-methylphenethyl azetidines.
The compound of this invention may be generally represented by the structural formula CH CH wherein R and R are the same J1 dilferent members of the group consisting of hydrogen, chlorine, fluorine and trifluoromethyl. In addition to the foregoing, R and R when taken together at the 3- and 4-positions respectively, may form a cycloalkyl ring having from 3 to 5 carbon atoms and when taken together at the 4- and 5-positions respectively, may form a methylenedioxy ring system. These compounds may be prepared as the free bases, or more conveniently, as the pharmaceutically acceptable acid-addition salts.
The term pharmaceutically acceptable acid-addition salts, as used herein, refers to the non-toxic salts which are prepared by reacting the free base with an organic or inorganic acid. Representative salts include the hydrochloride, hydrobromide, sulfate, bisulfate, acetate, valerate, oleate, laurate, borate, benzoate, lactate, phosphate, tosylate, citrate, maleate, 'fumarate, succinate, tartrate and the like.
Generally, these compounds are prepared by reacting an appropriately substituted a-methylphenethyl-3-halo-2, Z-disubstituted propionamide with a reducing agent in an inert solvent. This reaction results in a cyclization of the terminal portion of the molecule forming the azetidine compound. The disubstituted propionamide intermediate compounds have the general structural formula "nited States Patent O such N-substituted-3-halo-2,2-dimethyl may be prepared. Table I following below contains a few 3,649,618 Patented Mar. 14, 1972 ice wherein R and R are as previously defined and R is a member independently selected from the group consisting of alkyl and aryl. These compounds are prepared by reacting an appropriately substituted ct-methylphenethyl amine with a halo-2,2-disubstituted propionyl halide. The reac tion may be represented as follows:
wan
As indicated above, the intermediate compounds are prepared by reacting a substituted ot-methylphenethyl amine with a halo-2,2-disubstituted propionyl halide wherein the disubstitution may be with alkyl, aryl or an alkyl group and an aryl group on the 5 carbon atom. However, the propionyl halide derivative having methyl as each of the R substituents is most conveniently utilized since this acid is commercially available. It is to be understood, of course, that the reaction will proceed as set forth herein where each R is selected from either alkyl or aryl.
In order to more clearly illustrate the novel compounds of this invention, reference is made to the following examples which are intended to demonstrate but a few specific embodiments of the invention and not to limit the same thereby.
Example 1.3-chloro-2,2-dimethyl-N- [a-methyl-3- (trifluoromethyl phenethyl] propionamide To a chilled mixture of 40.5 grams (0.2 molar) of ozmethyl-3-trifiuoromethyl-phenethylamine, 20.2 grams (0.2 molar) of triethylamine and 500 ml. anhydrous ether is added 31.0 grams (0.2 molar) of fJ-chloropropionyl chloride dropwise with stirring. The mixture is stirred in the cold for 2 hours, washed twice with water, and the ether layer dried over anhydrous magnesium sulfate. The drying agent is removed, the ether stripped and the crude residue air-dried.
The crude product is further purifiedby taking same up in ether, washing the ethereal solution with 50 ml. of 3% hydrochloric acid, then with water, then with 50 ml. of 3% sodium hydroxide solution, and finally again with water. The ethereal solution is then' dried over anhydrous magnesium sulfate. The drying agent is removed, the ether stripped and a water-white residue crystallizes slowly on chilling; yielding 61.5 grams of 3-chloro-2,2-dimethyl-N- [ct-methyl 3 (trifluoromethyl)phenethyl]propionamide having a melting point of 5860 C.
Following the procedure of Example 1, various other propionamides representative species prepared in this manner, along With the identifying physical constants of each.
' TABLE 1 Analysis, percent Calculated Found Empirical M1. in
Ex. Compound formula C. H N C H N 3-ohloro2,2-dl methyl-N-[a-methyl-4-ohlorophenethyllproplonamide. CnHwClzNO 120.5-12L5 58.35 6.64 4.86 58.21 6.66 4.71 3-chloro-2,2-d1 methyl-N{a-methyl-3-ehlorophenethyl]propionamide OHH CIZNO 58.5-60.5 58.38 6.64 4.86 58.63 6.68 5.03
3-caililfigg22dimethyl-N-[mmethyl-3,4-(d1chloro)-phenethyl] propion- CnHisC e o 95-97 52-12 .3 3 A 5 3-chloro- 2,2'dimethyl-N-[a-methyl-4-fluorophenethyl] roplonamide. CHHIBCIFNO 77-79 61.88 7.05 5.15 61.56 7.07 4.96 3 chloro-2,2-dimethyl-N-{a-methyl-3-fiuoro-phenethyl propionamide.-. CnHmClFNO 81-845 61.88 7.04 5.15 61.65 7.08 5.28 7.-.... Elclgloro-Zfi-dimd ethyl-N-[a-methyl-t-(trifiuoromethyl)phenethyl1pro- CH1QC1F3NO 100-101 56.00 5. 96 4.35 56. 09 5. 90 4.38
ponarm e. 8 3-tgi lpria-2hm2-dimethyl-N-[a-methyl-4,E-(methylenedloxy)-phenethyl] CrsHzflClNOa 88-90 60.50 6.77 4.70 60.33 6.66 4.71
pon e. 9 3-chloro-N-[2(5-indanyl)-l-methylene]-2,2-dimethylproplonamide CllHflClFNO 113-114 69.49 8.23 4.76 69.42 8 02 4.86
Example l0.-1-(phenylisopropyl)-3,3-dimethylazetidine A solution of 37.2 grams (0.125 molar) of 3-bromo- 2,2-dimethyl-N[a-methylphenethyl]propionamide in 450 ml. of anhydrous ether is added dropwise to a suspension of 9.5 grams (0.25 molar) of lithium aluminum hydride in 100 ml. of anhydrous ether at a rate to maintain reflux, and stirred at room temperature for 5% hours. The lithium aluminum hydride complex and excess lithium aluminum hydride are decomposed of dropwise consecutive addition of 9 ml. of water, 9 ml. of 15% sodium hydroxide solution and 27 ml. of water to the chilled reaction mixture while stirring and the mixture is stirred for an additional A hour. The solid is removed by filtration and washed with ether. The combined filtrate and washings are dried over magnesium sulfate. After removing the drying agent, the ether is stripped and the residue distilled. A fraction having a boiling point of 88-115 C. at 1.5 mm. of pressure, N 1.4953 is obtained yielding a total of 28 grams of 1 (phenylisopropyl)-3,3-dimethyl azetidine. N.M.R. and LR. data confirmed the identity of the compound.
Following the procedure of Example 10, a number of other azetidine derivatives may be prepared having one or more radicals substituted on the phenyl ring. In Table fumarate, oxalate, and other such acid-addition salts may be prepared.
The free bases, as well as the acid-addition salts of the azetidine compounds, exhibit good activity as anorectic agents when administered orally or subcutaneously at dosages of between l-SO milligrams per kilogram of body weight. The test procedure utilized to illustrate this bio logical activity is relatively simple. Two groups consisting of four rats each are placed on a five-hour feeding schedule; that is, the total feeding period for a 24 hour period is 5 hours for each group at the same time of the day, seven days a week. Approximately /2 hour before the feeding time is to commence, the control group is administered a standard dosage of saline solution and the test group is administered a dosage of one of the test compounds. A measured amount of feed is given to both groups (the same amount for each group) and at the end of the 5 hour feeding period, the food remaining is measured to determine intake.
In Table III following below is given the activity data found for a representative number of the compounds of this invention. In each case, the percentage figure represents the percent of food intake less than the controls at the expressed dosage level.
TABLE III Percent intake Dosage, less than LD Compound mgJkg. controls mgJkg.
3 51 10 59 1. l-(phenylisopropyl)-3,3-dimethyl azetidine-HCI g. g; 300
82 2. l-(tehlorophenylisopropyl)-3,3-dimethy1 azatidine'HCl ,3 g; 500 3. 1-(3,4-dichlorophenylisopropyl)-3,3-dimethyl azetidine- H01 12 13 300 4. l-(Mluorophenylisopropyl)-3,3-dimethyl azetrdine-HCI. 10 28 500 5. 1-(4-fiuorophenylisopropyl)-3'dimethyl azetidme- H01- 10 21 300 6. 1-(4-trifluoromethyl phenylisopropyl)-3,3-d1rnethyl azetidm 14 26 750 II below are listed a representative number of other such azetidines prepared from the correspondingly substituted 3-halo-2,Z-dimethyl-phenethyl propionamide along the identifying physical constants of each. In each case, N.M.R. and LR. data confirmed the identity of the compound.
The column headed LD mg./kg. in Table 111 above, indicates the oral disage in milligrams per kilogram of body weight, which is lethal to 50% of the test animals. In the above experiment, the test compounds were administered via the oral route, although other routes of administration, such as subcutaneous, intraperitoneal, and intra- TABLE II Analysis Calculated Found Empirical Compound formula B.P. 111C. 0 H N H N 1-(4-chlorophenylisopropyl)-3,3-dimethyl azetidine CnHmOlN 110-124 at 1.1 mm. pressure..- 70.72 8. 48 5. 89 70. 74 8.71 5.7 1-(3-ohlorophenylisopropyl)-3,3-dimethylazetidine..- CHHMOIN 116120at1.9rnm.pressure. 70.72 8.48 5. 89 70. 99 8.62 5. 99 1-(3,4-diehlorophenylisopropyl)-3,3-dimethylazetidine. OnHnClzN138141at1.5mm.pressure 61.78 7.03 5.14 61.60 7.09 5.25 '1-(4-fiuorophenylisopropyl) 3,3-dlmethylazetidine-.. CnH FN 8791at1.5mm.pressure. 75.98 9.11 6.33 75.69 9.13 6.53 1-(3-fiuorophenylisopropyl)-3,3-dirnethyl azetidine CuHmFN 87-90 at 1.4mm.prcssure.- 75.98 9.11 6. 33 70. 69 9.14 6.43 1-(4-trifluoromethylphenyl isopropyl)-8,3-dimethyl azetidine..- CisHznFaN 97-103 at 1.3 mm. pressure 66.40 7. 43 5.16 65.84 7. 68 5.41 1-(3-trifiuoromethylphenyl1sopropyl)-3,3-dimethyl azetidine.-- CuHzoFaN 93-103 at 2.0 mm.pfessure 66.40 7.43 5.16 66.17 7.43 5. 29 1-(4-5-methyleuedioxy-phenyl isopropyl)-3,3-dimethyl azetidine CmHzrNOz 136-142at1.3mm.pressure.. 72.84 8.56 5.66 72.75 8.33 5.69 19 1-[2(5-indanyl)-1-methyleneethyl]-3,3-dimethylazetidine CnHnN 133-137 at 1.3 mm. pressu e... 83. 90 10.3 5 5. 83.65 10. 49 5.83
muscular, among others, may be successfully employed. Furthermore, the compounds were administered in the form of their hydrochloride acid-addition salts for the reason that these salts are very water-soluble and therefore CH CH CH-N l CH wherein R and R are each members independently selected from the group consisting of hydrogen, chlorine, fluorine, trifluoromethyl, and R and R taken together at the 4- and 5-positions forming a methylene dioxy ring, and R and R taken together at the 3- and 4-positions forming a cycloalkyl ring having from 3 to 5 carbon atoms; and the pharmaceutically acceptable acid-addition salts thereof.
2. A compound according to claim 1 wherein R and R are each hydrogen.
3. A compound according to claim 1 wherein R is hydrogen and R is 4-chloro.
4. The compounds according to claim 1 wherein the acid-addition salt is hydrochloride salt.
ALTON D. ROLLINS, Primary Examiner U.S. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7775470A | 1970-10-02 | 1970-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3649618A true US3649618A (en) | 1972-03-14 |
Family
ID=22139872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US77754A Expired - Lifetime US3649618A (en) | 1970-10-02 | 1970-10-02 | Certain 1-aralkyl azetidines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3649618A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4529544A (en) * | 1982-03-15 | 1985-07-16 | The Dow Chemical Company | Formation of azetidines by decarboxylation of tetrahydro-1,3-oxazin-2-ones |
| US4560507A (en) * | 1983-05-04 | 1985-12-24 | Shell Oil Company | Preparation of 1-benzylazetidin-3-ol |
| EP0279543A1 (en) * | 1987-01-28 | 1988-08-24 | A.H. ROBINS COMPANY, INCORPORATED (a Delaware corporation) | Process for the preparation of an azetidine and intermediates therefor |
-
1970
- 1970-10-02 US US77754A patent/US3649618A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4529544A (en) * | 1982-03-15 | 1985-07-16 | The Dow Chemical Company | Formation of azetidines by decarboxylation of tetrahydro-1,3-oxazin-2-ones |
| US4560507A (en) * | 1983-05-04 | 1985-12-24 | Shell Oil Company | Preparation of 1-benzylazetidin-3-ol |
| EP0279543A1 (en) * | 1987-01-28 | 1988-08-24 | A.H. ROBINS COMPANY, INCORPORATED (a Delaware corporation) | Process for the preparation of an azetidine and intermediates therefor |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1482522A3 (en) | Method of producing substituted 1-(1-phenylcyclobutyl)-alkylamines or their pharmaceutically acceptable salts | |
| KR880002310B1 (en) | Process for producing phenethanol amines | |
| US3532749A (en) | N'-propargyl-n**2-cyclopropyl-ethylenediamines and the salts thereof | |
| US4423044A (en) | 3,4-Dihydro-5H-2,3-benzodiazepine derivatives and pharmaceutical use thereof | |
| IMMEDIATA et al. | β-Naphthyl derivatives of ethanolamine and n-substituted ethanolamines | |
| US3117128A (en) | Certificate of correction | |
| JPS6051174A (en) | Manufacture of novel arylpiperidine derivative | |
| US3365458A (en) | N-aryl-n'-cyclopropyl-ethylene diamine derivatives | |
| CA2007127A1 (en) | Piperidines, process for their preparation and drugs containing same | |
| US4048314A (en) | Morpholino containing 4-arylpiperidine derivatives | |
| GB1576007A (en) | Hypolipidaemic compositions | |
| EP0102194B1 (en) | 3-phenoxy-1-azetidinecarboxamides and their use and preparation | |
| EP0226516B1 (en) | Amide derivatives and antiallergic agents containing the same | |
| US3649618A (en) | Certain 1-aralkyl azetidines | |
| US4139538A (en) | Oxazolidinones as therapeutic agents | |
| US4499286A (en) | Derivatives of thienylacetic acid amides and their pharmaceutically acceptable acid salts and a process for the preparation thereof | |
| US3733339A (en) | Disubstituted propionamides | |
| US3580910A (en) | P-alkoxy-piperidine-amides | |
| CA1133495A (en) | Cis and trans-3-aryloxy-4- hydroxypyrrolidines and derivatives thereof | |
| US3754000A (en) | Derivatives of 3-aminocarbonyl-2-oxazolidinone and their process of preparation | |
| US3972935A (en) | Antiarrhythmic agents | |
| US3213138A (en) | N, n-disubstituted-n'-phenylalkyl hydrazines | |
| US4603138A (en) | Amine derivatives | |
| US4179442A (en) | 4-(Alpha-hydroxy-isopropyl)-5-phenyl-oxazolidin-2-one | |
| US4105795A (en) | Antispasmodic substituted sulphoximides |